Ethyl 3-[7-(N-acetyl-4-meth-oxy-benzene-sulfonamido)-3-chloro-2H-indazol-2-yl]propionate.

In the title compound, C21H22ClN3O6S, the fused five- and six-membered ring rings are almost perpendicular to the planes through the atoms forming the acetyl and the propionic ester groups, as indicated by the dihedral angles of 80.3 (2) and 88.3 (7)°, respectively. The dihedral angle between the indazole system and the 4-meth-oxy-benzene-sulfonyl group is 13.76 (6)°. The carbonyl O atom is split over two positions in a 0.60 (5):0.40 (5) ratio. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯N inter-actions into a three-dimensional network.

Related literature

For the biological activity of sulfonamides, see: Lohou et al. (2012 ▶); Salerno et al. (2012 ▶); Kaltenbach et al. (2003 ▶); Thangadurai et al. (2012 ▶); Abbassi et al. (2012 ▶). For similar compounds, see: Abbassi et al. (2013 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C21H22ClN3O6S

M = 479.93

Triclinic,

a = 9.1442 (3) Å

b = 9.4376 (4) Å

c = 14.0931 (6) Å

α = 108.262 (2)°

β = 96.017 (2)°

γ = 103.313 (2)°

V = 1103.12 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.38 × 0.32 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.700, T max = 0.746

26786 measured reflections

6725 independent reflections

4687 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.02

6725 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814003183/tk5294sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003183/tk5294Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003183/tk5294Isup3.cml

CCDC reference: 986487

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H22ClN3O6S	Z = 2
Mr = 479.93	F(000) = 500
Triclinic, P1	Dx = 1.445 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1442 (3) Å	Cell parameters from 6725 reflections
b = 9.4376 (4) Å	θ = 2.4–30.5°
c = 14.0931 (6) Å	µ = 0.31 mm−1
α = 108.262 (2)°	T = 296 K
β = 96.017 (2)°	Block, colourless
γ = 103.313 (2)°	0.38 × 0.32 × 0.27 mm
V = 1103.12 (8) Å3

Bruker X8 APEX diffractometer	6725 independent reflections
Radiation source: fine-focus sealed tube	4687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 30.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.700, Tmax = 0.746	k = −13→12
26786 measured reflections	l = −19→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.2297P] where P = (Fo2 + 2Fc2)/3
6725 reflections	(Δ/σ)max < 0.001
299 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	1.0486 (3)	0.8525 (3)	0.54237 (17)	0.0722 (6)
H1A	1.0445	0.9308	0.6042	0.108*
H1B	1.0923	0.9013	0.4975	0.108*
H1C	1.1106	0.7903	0.5579	0.108*
C2	0.8924 (3)	0.7528 (3)	0.49251 (17)	0.0745 (6)
H2A	0.8474	0.7029	0.5373	0.089*
H2B	0.8285	0.8150	0.4774	0.089*
C3	0.8483 (2)	0.4891 (2)	0.38663 (16)	0.0538 (4)
C4	0.8705 (2)	0.3834 (2)	0.28825 (15)	0.0522 (4)
H4A	0.8013	0.2809	0.2726	0.063*
H4B	0.9742	0.3743	0.2970	0.063*
C5	0.84382 (17)	0.43617 (19)	0.19883 (13)	0.0449 (4)
H5A	0.9164	0.5362	0.2122	0.054*
H5B	0.8617	0.3625	0.1387	0.054*
C6	0.64292 (16)	0.56845 (16)	0.16545 (11)	0.0358 (3)
C7	0.48449 (16)	0.52038 (16)	0.13433 (11)	0.0345 (3)
C8	0.44533 (15)	0.36588 (15)	0.13440 (11)	0.0327 (3)
C9	0.28989 (16)	0.27675 (16)	0.10605 (11)	0.0355 (3)
C10	0.18252 (17)	0.34113 (19)	0.07555 (13)	0.0435 (4)
H10	0.0804	0.2829	0.0551	0.052*
C11	0.2236 (2)	0.4947 (2)	0.07452 (13)	0.0477 (4)
H11	0.1477	0.5347	0.0529	0.057*
C12	0.37178 (19)	0.58583 (18)	0.10434 (12)	0.0429 (3)
H12	0.3973	0.6873	0.1048	0.051*
C13	0.25249 (17)	−0.01017 (17)	0.03603 (12)	0.0423 (3)
C14	0.3172 (2)	0.01302 (19)	−0.05230 (13)	0.0488 (4)
H14A	0.4034	0.1038	−0.0286	0.073*
H14B	0.2405	0.0264	−0.0981	0.073*
H14C	0.3494	−0.0761	−0.0872	0.073*
C15	0.28344 (17)	0.00934 (18)	0.26812 (12)	0.0426 (3)
C16	0.4413 (2)	0.0666 (2)	0.29788 (16)	0.0613 (5)
H16	0.4928	0.1571	0.2887	0.074*
C17	0.5205 (2)	−0.0119 (3)	0.34089 (19)	0.0711 (6)
H17	0.6266	0.0248	0.3596	0.085*
C18	0.4447 (2)	−0.1454 (2)	0.35699 (14)	0.0516 (4)
C19	0.2880 (2)	−0.2002 (2)	0.32867 (15)	0.0548 (4)
H19	0.2360	−0.2887	0.3400	0.066*
C20	0.20833 (19)	−0.1236 (2)	0.28343 (16)	0.0552 (5)
H20	0.1025	−0.1620	0.2630	0.066*
C21	0.4639 (3)	−0.3534 (3)	0.4150 (2)	0.0850 (7)
H21A	0.3928	−0.3336	0.4597	0.127*
H21B	0.5405	−0.3892	0.4452	0.127*
H21C	0.4103	−0.4315	0.3510	0.127*
N1	0.68752 (13)	0.44938 (14)	0.17929 (9)	0.0359 (3)
N2	0.56842 (13)	0.32172 (13)	0.16155 (10)	0.0366 (3)
N3	0.24731 (14)	0.12398 (13)	0.11297 (10)	0.0388 (3)
O1	0.90147 (18)	0.63540 (16)	0.39826 (10)	0.0687 (4)
O2A	0.827 (4)	0.460 (2)	0.4645 (11)	0.074 (4)	0.40 (5)
O2B	0.763 (3)	0.4365 (10)	0.433 (2)	0.097 (5)	0.60 (5)
O3	0.20543 (16)	−0.13637 (13)	0.04358 (10)	0.0594 (3)
O4	0.21707 (17)	0.26817 (15)	0.28507 (11)	0.0632 (4)
O5	0.02109 (13)	0.02348 (18)	0.18811 (13)	0.0709 (4)
O6	0.53520 (17)	−0.21420 (19)	0.39901 (13)	0.0750 (4)
S1	0.17842 (4)	0.11051 (5)	0.21770 (4)	0.04718 (12)
Cl1	0.76852 (5)	0.74258 (5)	0.18505 (4)	0.05352 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0799 (15)	0.0598 (12)	0.0636 (13)	0.0125 (11)	−0.0014 (11)	0.0131 (10)
C2	0.0808 (15)	0.0679 (14)	0.0560 (12)	0.0081 (11)	0.0137 (11)	0.0050 (10)
C3	0.0460 (9)	0.0567 (11)	0.0697 (12)	0.0192 (8)	0.0124 (8)	0.0329 (9)
C4	0.0395 (8)	0.0446 (9)	0.0715 (12)	0.0145 (7)	0.0029 (8)	0.0193 (8)
C5	0.0288 (7)	0.0433 (8)	0.0569 (10)	0.0070 (6)	0.0096 (6)	0.0117 (7)
C6	0.0376 (7)	0.0283 (7)	0.0378 (7)	0.0020 (5)	0.0082 (6)	0.0115 (5)
C7	0.0369 (7)	0.0280 (6)	0.0366 (7)	0.0069 (5)	0.0079 (6)	0.0099 (5)
C8	0.0319 (7)	0.0262 (6)	0.0379 (7)	0.0070 (5)	0.0084 (5)	0.0088 (5)
C9	0.0305 (6)	0.0278 (6)	0.0434 (8)	0.0054 (5)	0.0076 (6)	0.0078 (5)
C10	0.0316 (7)	0.0413 (8)	0.0528 (9)	0.0101 (6)	0.0055 (6)	0.0106 (7)
C11	0.0443 (9)	0.0453 (9)	0.0557 (10)	0.0208 (7)	0.0054 (7)	0.0159 (7)
C12	0.0506 (9)	0.0329 (7)	0.0484 (9)	0.0156 (6)	0.0094 (7)	0.0157 (6)
C13	0.0380 (8)	0.0296 (7)	0.0484 (9)	0.0052 (6)	−0.0055 (6)	0.0063 (6)
C14	0.0582 (10)	0.0387 (8)	0.0445 (9)	0.0178 (7)	0.0012 (7)	0.0072 (7)
C15	0.0344 (7)	0.0408 (8)	0.0494 (9)	0.0031 (6)	0.0109 (6)	0.0155 (7)
C16	0.0376 (9)	0.0613 (12)	0.0818 (14)	−0.0078 (8)	0.0013 (9)	0.0393 (10)
C17	0.0359 (9)	0.0798 (15)	0.0981 (16)	−0.0058 (9)	−0.0025 (9)	0.0521 (13)
C18	0.0457 (9)	0.0578 (11)	0.0535 (10)	0.0098 (8)	0.0101 (7)	0.0253 (8)
C19	0.0460 (9)	0.0487 (10)	0.0719 (12)	0.0050 (7)	0.0163 (8)	0.0282 (9)
C20	0.0339 (8)	0.0500 (10)	0.0798 (13)	0.0009 (7)	0.0107 (8)	0.0277 (9)
C21	0.0747 (15)	0.0906 (18)	0.117 (2)	0.0263 (13)	0.0257 (14)	0.0693 (16)
N1	0.0290 (6)	0.0305 (6)	0.0447 (7)	0.0029 (4)	0.0062 (5)	0.0124 (5)
N2	0.0291 (6)	0.0274 (6)	0.0511 (7)	0.0045 (4)	0.0076 (5)	0.0130 (5)
N3	0.0328 (6)	0.0280 (6)	0.0501 (7)	0.0027 (5)	0.0085 (5)	0.0102 (5)
O1	0.0901 (11)	0.0518 (8)	0.0469 (7)	−0.0014 (7)	0.0122 (7)	0.0092 (6)
O2A	0.090 (8)	0.069 (5)	0.079 (5)	0.023 (5)	0.029 (5)	0.044 (3)
O2B	0.106 (9)	0.078 (3)	0.117 (9)	0.013 (4)	0.069 (8)	0.041 (4)
O3	0.0734 (9)	0.0294 (6)	0.0623 (8)	0.0020 (5)	−0.0003 (6)	0.0112 (5)
O4	0.0792 (9)	0.0511 (7)	0.0686 (8)	0.0254 (7)	0.0410 (7)	0.0198 (6)
O5	0.0303 (6)	0.0794 (10)	0.1197 (12)	0.0092 (6)	0.0205 (7)	0.0597 (9)
O6	0.0554 (8)	0.0882 (11)	0.0985 (12)	0.0154 (7)	0.0105 (8)	0.0603 (10)
S1	0.03440 (19)	0.0441 (2)	0.0676 (3)	0.00900 (16)	0.02084 (18)	0.02352 (19)
Cl1	0.0495 (2)	0.0355 (2)	0.0679 (3)	−0.00609 (16)	0.00440 (19)	0.02249 (18)

C1—C2	1.475 (3)	C11—H11	0.9300
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—O3	1.2116 (19)
C1—H1C	0.9600	C13—N3	1.3996 (19)
C2—O1	1.464 (2)	C13—C14	1.488 (2)
C2—H2A	0.9700	C14—H14A	0.9600
C2—H2B	0.9700	C14—H14B	0.9600
C3—O2B	1.193 (6)	C14—H14C	0.9600
C3—O2A	1.233 (10)	C15—C20	1.377 (2)
C3—O1	1.305 (2)	C15—C16	1.387 (2)
C3—C4	1.498 (3)	C15—S1	1.7446 (18)
C4—C5	1.510 (3)	C16—C17	1.370 (3)
C4—H4A	0.9700	C16—H16	0.9300
C4—H4B	0.9700	C17—C18	1.389 (3)
C5—N1	1.4680 (19)	C17—H17	0.9300
C5—H5A	0.9700	C18—O6	1.357 (2)
C5—H5B	0.9700	C18—C19	1.375 (2)
C6—N1	1.3413 (19)	C19—C20	1.377 (3)
C6—C7	1.392 (2)	C19—H19	0.9300
C6—Cl1	1.6959 (14)	C20—H20	0.9300
C7—C12	1.410 (2)	C21—O6	1.423 (3)
C7—C8	1.4194 (19)	C21—H21A	0.9600
C8—N2	1.3464 (18)	C21—H21B	0.9600
C8—C9	1.4168 (18)	C21—H21C	0.9600
C9—C10	1.367 (2)	N1—N2	1.3602 (15)
C9—N3	1.4412 (18)	N3—S1	1.6932 (14)
C10—C11	1.416 (2)	O4—S1	1.4292 (13)
C10—H10	0.9300	O5—S1	1.4260 (13)
C11—C12	1.367 (2)
C2—C1—H1A	109.5	C7—C12—H12	121.2
C2—C1—H1B	109.5	O3—C13—N3	120.00 (16)
H1A—C1—H1B	109.5	O3—C13—C14	123.63 (15)
C2—C1—H1C	109.5	N3—C13—C14	116.37 (13)
H1A—C1—H1C	109.5	C13—C14—H14A	109.5
H1B—C1—H1C	109.5	C13—C14—H14B	109.5
O1—C2—C1	108.42 (19)	H14A—C14—H14B	109.5
O1—C2—H2A	110.0	C13—C14—H14C	109.5
C1—C2—H2A	110.0	H14A—C14—H14C	109.5
O1—C2—H2B	110.0	H14B—C14—H14C	109.5
C1—C2—H2B	110.0	C20—C15—C16	119.85 (17)
H2A—C2—H2B	108.4	C20—C15—S1	119.72 (13)
O2B—C3—O2A	30.9 (5)	C16—C15—S1	120.34 (13)
O2B—C3—O1	126.8 (4)	C17—C16—C15	119.22 (16)
O2A—C3—O1	116.2 (10)	C17—C16—H16	120.4
O2B—C3—C4	119.1 (8)	C15—C16—H16	120.4
O2A—C3—C4	128.4 (6)	C16—C17—C18	120.96 (17)
O1—C3—C4	112.24 (16)	C16—C17—H17	119.5
C3—C4—C5	114.43 (15)	C18—C17—H17	119.5
C3—C4—H4A	108.7	O6—C18—C19	124.74 (17)
C5—C4—H4A	108.7	O6—C18—C17	115.74 (16)
C3—C4—H4B	108.7	C19—C18—C17	119.50 (18)
C5—C4—H4B	108.7	C18—C19—C20	119.67 (16)
H4A—C4—H4B	107.6	C18—C19—H19	120.2
N1—C5—C4	111.86 (13)	C20—C19—H19	120.2
N1—C5—H5A	109.2	C19—C20—C15	120.77 (15)
C4—C5—H5A	109.2	C19—C20—H20	119.6
N1—C5—H5B	109.2	C15—C20—H20	119.6
C4—C5—H5B	109.2	O6—C21—H21A	109.5
H5A—C5—H5B	107.9	O6—C21—H21B	109.5
N1—C6—C7	108.02 (12)	H21A—C21—H21B	109.5
N1—C6—Cl1	122.44 (11)	O6—C21—H21C	109.5
C7—C6—Cl1	129.55 (12)	H21A—C21—H21C	109.5
C6—C7—C12	135.94 (14)	H21B—C21—H21C	109.5
C6—C7—C8	102.85 (13)	C6—N1—N2	112.93 (12)
C12—C7—C8	121.18 (13)	C6—N1—C5	128.36 (12)
N2—C8—C9	127.74 (13)	N2—N1—C5	118.31 (12)
N2—C8—C7	112.71 (12)	C8—N2—N1	103.47 (11)
C9—C8—C7	119.54 (13)	C13—N3—C9	123.30 (13)
C10—C9—C8	118.45 (13)	C13—N3—S1	120.09 (11)
C10—C9—N3	121.44 (13)	C9—N3—S1	116.51 (10)
C8—C9—N3	120.08 (13)	C3—O1—C2	118.52 (17)
C9—C10—C11	121.33 (14)	C18—O6—C21	118.14 (16)
C9—C10—H10	119.3	O5—S1—O4	118.40 (9)
C11—C10—H10	119.3	O5—S1—N3	109.15 (8)
C12—C11—C10	121.85 (15)	O4—S1—N3	103.71 (7)
C12—C11—H11	119.1	O5—S1—C15	109.27 (8)
C10—C11—H11	119.1	O4—S1—C15	109.37 (9)
C11—C12—C7	117.60 (14)	N3—S1—C15	106.18 (7)
C11—C12—H12	121.2
O2B—C3—C4—C5	126 (2)	C7—C6—N1—C5	171.20 (14)
O2A—C3—C4—C5	161.7 (19)	Cl1—C6—N1—C5	−8.9 (2)
O1—C3—C4—C5	−39.5 (2)	C4—C5—N1—C6	130.76 (16)
C3—C4—C5—N1	−59.63 (19)	C4—C5—N1—N2	−57.11 (18)
N1—C6—C7—C12	−176.92 (16)	C9—C8—N2—N1	179.12 (14)
Cl1—C6—C7—C12	3.2 (3)	C7—C8—N2—N1	0.16 (16)
N1—C6—C7—C8	1.25 (15)	C6—N1—N2—C8	0.70 (16)
Cl1—C6—C7—C8	−178.68 (12)	C5—N1—N2—C8	−172.61 (13)
C6—C7—C8—N2	−0.88 (16)	O3—C13—N3—C9	−175.04 (14)
C12—C7—C8—N2	177.63 (13)	C14—C13—N3—C9	4.8 (2)
C6—C7—C8—C9	−179.94 (13)	O3—C13—N3—S1	1.2 (2)
C12—C7—C8—C9	−1.4 (2)	C14—C13—N3—S1	−179.00 (11)
N2—C8—C9—C10	−176.42 (14)	C10—C9—N3—C13	97.10 (18)
C7—C8—C9—C10	2.5 (2)	C8—C9—N3—C13	−85.05 (18)
N2—C8—C9—N3	5.7 (2)	C10—C9—N3—S1	−79.22 (17)
C7—C8—C9—N3	−175.44 (12)	C8—C9—N3—S1	98.63 (14)
C8—C9—C10—C11	−1.6 (2)	O2B—C3—O1—C2	18 (2)
N3—C9—C10—C11	176.25 (14)	O2A—C3—O1—C2	−16.5 (14)
C9—C10—C11—C12	−0.4 (3)	C4—C3—O1—C2	−178.05 (17)
C10—C11—C12—C7	1.5 (2)	C1—C2—O1—C3	121.8 (2)
C6—C7—C12—C11	177.37 (16)	C19—C18—O6—C21	0.2 (3)
C8—C7—C12—C11	−0.5 (2)	C17—C18—O6—C21	−178.6 (2)
C20—C15—C16—C17	1.0 (3)	C13—N3—S1—O5	−63.19 (14)
S1—C15—C16—C17	177.49 (17)	C9—N3—S1—O5	113.25 (12)
C15—C16—C17—C18	−1.4 (3)	C13—N3—S1—O4	169.72 (12)
C16—C17—C18—O6	179.3 (2)	C9—N3—S1—O4	−13.83 (13)
C16—C17—C18—C19	0.5 (3)	C13—N3—S1—C15	54.49 (13)
O6—C18—C19—C20	−177.76 (18)	C9—N3—S1—C15	−129.06 (11)
C17—C18—C19—C20	0.9 (3)	C20—C15—S1—O5	−6.70 (18)
C18—C19—C20—C15	−1.4 (3)	C16—C15—S1—O5	176.77 (16)
C16—C15—C20—C19	0.4 (3)	C20—C15—S1—O4	124.38 (15)
S1—C15—C20—C19	−176.12 (15)	C16—C15—S1—O4	−52.16 (17)
C7—C6—N1—N2	−1.29 (17)	C20—C15—S1—N3	−124.30 (15)
Cl1—C6—N1—N2	178.64 (10)	C16—C15—S1—N3	59.16 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4i	0.97	2.58	3.438 (3)	148
C21—H21A···O2Bii	0.96	2.44	3.273 (7)	144
C21—H21A···O2Aii	0.96	2.60	3.43 (2)	145
C2—H2B···O6iii	0.97	2.71	3.510 (3)	140
C14—H14C···N2iv	0.96	2.55	3.501 (2)	173
C14—H14B···O5v	0.96	2.45	3.348 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4i	0.97	2.58	3.438 (3)	148
C21—H21A⋯O2B ii	0.96	2.44	3.273 (7)	144
C21—H21A⋯O2A ii	0.96	2.60	3.43 (2)	145
C2—H2B⋯O6iii	0.97	2.71	3.510 (3)	140
C14—H14C⋯N2iv	0.96	2.55	3.501 (2)	173
C14—H14B⋯O5v	0.96	2.45	3.348 (2)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .